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This predominantly involves very expensive noble metals such as iridium, platinum or else gold.
Moreover, a large number of OLED emitter materials known to date are ecologically problematic, so that the use of less toxic materials is desirable, such as copper(I) complexes.
Consequently, further charge carrier streams can no longer lead completely to the occupation of the excited and emitting states.
The result is then unwanted ohmic losses.
This leads to a distinct decline in efficiency of the OLED device with rising current density (called “roll-off” behavior).
For instance, disadvantages are found particularly in the case of use of emitters with long emission lifetimes for OLED illuminations where a high luminance, for example of more than 1000 cd/m2, is required (cf.
Furthermore,
Method used
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example 1
1,10-Phenanthroline Ligands that Increase Solubility in Nonpolar Solvents
[0112]4,7-dichloro-2,9-dimethyl-1,10-phenanthroline, Phen1, is synthesized according to the literature (M. Schmittel, H. Ammon Eur. J. Org. Chem. 1998, 785.). For the substitution with a n-butyl group, an equimolar amount of n-HexMgBr and CuBr is added. The purification of Phen2 is done using column chromatography over silica gel.
[0113]The phenanthroline-dichloride Phen3 is synthesized according to (M. Schmittel, H Ammon Eur. J. Org. Chem. 1998, 785.). The synthesis of Phen4 is performed analogously to Phen2.
[0114]2,4,7,9-tetra-methyl-1,10-phenanthroline, Phen5, is synthesized according to (G. Butt, R. D. Topsom, J. Heterocyclic Chem. 1981, 18, 641). 2,4,7,9-Tetrabromomethylen-1,10-phenanthroline, Phen6, is synthesized via side chain bromation using NBS and isolated by column chromatography (SiO2). The reaction with n-HexLi leads to Phen7.
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Abstract
The invention relates to neutral mononuclear copper (I) complexes for emitting light and with a structure according to formula (A) in which: M represents: Cu(I); L∩L represents: a single, negatively charged, bidentate ligand; N∩N represents: a diimine ligand (substituted with R and FG), in particular a substituted 2,2′-bipyridine derivative (bpy) or a substituted 1,10-phenanthroline derivative (phen); R represents: at least one sterically demanding substituent for preventing the planarisation of the complex in the excited state; FG=functional group, and represents: at least one second substituent for increasing solubility in organic solvents. The substituent can also be used for electron transport or alternatively for hole transport, said functional group being bound to the diimine ligands either directly or by means of suitable bridges; and the copper (I) complex: having a ΔE(S1−T1) value of less than 2500 cm−1 between the lowest excited singlet state (S1) and the triplet state (T1) which lies below; having an emission lifespan of at most 20 μs; having an emission quantum yield of greater than 40%, and a solubility of at least 1 g/L in organic solvents, in particular polar organic hydrocarbons such as acetone, methyl ethyl ketone, benzene, toluene, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, dichloroethane, tetrachloroethylene, alcohols, acetonitrile or water.
Description
[0001]The present invention relates to the use of soluble copper(I) complexes (Cu(I)-complexes) as emitters in OLEDs (organic light-emitting diodes) and in other optoelectronic devices.INTRODUCTION[0002]A dramatic change is currently on the horizon in the field of visual display and illumination technology. It will be possible to manufacture flat displays or illuminated surfaces having a thickness of less than 0.5 mm. These are notable for many fascinating properties. For example, it will be possible to achieve illuminated surfaces in the form of wallpaper with very low energy consumption. It is also of particular interest that color visual display units will be producible with hitherto unachievable colorfastness, brightness and viewing angle independence, with low weight and with very low power consumption. It will be possible to configure the visual display units as micro-displays or large visual display units of several square meters in area in rigid form or flexibly, or else as ...
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